CA1299183C - 1h-pyrrolo ¬3,2-c|pyridines and their preparation - Google Patents
1h-pyrrolo ¬3,2-c|pyridines and their preparationInfo
- Publication number
- CA1299183C CA1299183C CA000497380A CA497380A CA1299183C CA 1299183 C CA1299183 C CA 1299183C CA 000497380 A CA000497380 A CA 000497380A CA 497380 A CA497380 A CA 497380A CA 1299183 C CA1299183 C CA 1299183C
- Authority
- CA
- Canada
- Prior art keywords
- pyrrolo
- pyridine
- group
- formula
- benzenesulphonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title abstract description 21
- 150000003222 pyridines Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 39
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims abstract description 31
- SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical group N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 22
- -1 alkyl lithium Chemical compound 0.000 claims abstract description 20
- 238000006138 lithiation reaction Methods 0.000 claims abstract description 16
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000006239 protecting group Chemical group 0.000 claims abstract description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- SZWRAMOZOIVPDO-UHFFFAOYSA-N [Li]C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 Chemical compound [Li]C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 SZWRAMOZOIVPDO-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 8
- RUXJRMOMZYQAOY-UHFFFAOYSA-N N1=CC=C2N(C(=O)OC(C)(C)C)C([Li])=CC2=C1 Chemical compound N1=CC=C2N(C(=O)OC(C)(C)C)C([Li])=CC2=C1 RUXJRMOMZYQAOY-UHFFFAOYSA-N 0.000 claims description 7
- 150000002641 lithium Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- UBBYLODQCKBACW-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)pyrrolo[3,2-c]pyridin-2-yl]ethanone Chemical compound CC(=O)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 UBBYLODQCKBACW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- JXCHTSUBCBYZAV-UHFFFAOYSA-N 1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine Chemical compound C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 JXCHTSUBCBYZAV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 230000016507 interphase Effects 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- XCXLZQHXEWBHFW-UHFFFAOYSA-N [1-(benzenesulfonyl)pyrrolo[3,2-c]pyridin-2-yl]-trimethylsilane Chemical compound C[Si](C)(C)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 XCXLZQHXEWBHFW-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 229960004424 carbon dioxide Drugs 0.000 claims description 3
- 235000011089 carbon dioxide Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- PKYJYPDHSCLTJO-UHFFFAOYSA-N tert-butyl pyrrolo[3,2-c]pyridine-1-carboxylate Chemical compound N1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 PKYJYPDHSCLTJO-UHFFFAOYSA-N 0.000 claims description 3
- YWUITRZFOVMHTI-UHFFFAOYSA-N 1-(benzenesulfonyl)-n,n-diethylpyrrolo[3,2-c]pyridine-2-carboxamide Chemical compound CCN(CC)C(=O)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 YWUITRZFOVMHTI-UHFFFAOYSA-N 0.000 claims description 2
- FQFPADLBRGOSJT-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)pyrrolo[3,2-c]pyridin-2-yl]ethanol Chemical compound CC(O)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 FQFPADLBRGOSJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DUJMMZTVJNSXHM-UHFFFAOYSA-N tert-butyl 2-[hydroxy(phenyl)methyl]pyrrolo[3,2-c]pyridine-1-carboxylate Chemical compound C=1C2=CN=CC=C2N(C(=O)OC(C)(C)C)C=1C(O)C1=CC=CC=C1 DUJMMZTVJNSXHM-UHFFFAOYSA-N 0.000 claims description 2
- SOCJFQORAIXLEZ-UHFFFAOYSA-N tert-butyl 2-trimethylsilylpyrrolo[3,2-c]pyridine-1-carboxylate Chemical compound N1=CC=C2N(C(=O)OC(C)(C)C)C([Si](C)(C)C)=CC2=C1 SOCJFQORAIXLEZ-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- XWSMSOYZRPLLIV-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-ethylpyrrolo[3,2-c]pyridine Chemical compound CCC1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 XWSMSOYZRPLLIV-UHFFFAOYSA-N 0.000 claims 1
- BOVXSSYSWCHQMX-UHFFFAOYSA-N 1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine-2-carbaldehyde Chemical compound O=CC1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 BOVXSSYSWCHQMX-UHFFFAOYSA-N 0.000 claims 1
- GKEIPZOHINOXNF-UHFFFAOYSA-N 1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 GKEIPZOHINOXNF-UHFFFAOYSA-N 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- TVFKHEJIMYUDLP-UHFFFAOYSA-N ethyl 1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 TVFKHEJIMYUDLP-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- TVWVMHCJHKWGTN-UHFFFAOYSA-N methyl 1-(benzenesulfonyl)pyrrolo[3,2-c]pyridine-2-carboxylate Chemical compound COC(=O)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 TVWVMHCJHKWGTN-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 7
- 230000000507 anthelmentic effect Effects 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 241000786363 Rhampholeon spectrum Species 0.000 description 22
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical compound [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002642 lithium compounds Chemical class 0.000 description 3
- 238000006263 metalation reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000005255 pyrrolopyridines Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- JXCHTSUBCBYZAV-QOWOAITPSA-N 1-(benzenesulfonyl)-2-deuteriopyrrolo[3,2-c]pyridine Chemical compound [2H]C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 JXCHTSUBCBYZAV-QOWOAITPSA-N 0.000 description 1
- MOCVPCBCMCSIFA-UHFFFAOYSA-N 1-[1-(benzenesulfonyl)pyrrolo[3,2-c]pyridin-2-yl]-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)(C)C1=CC2=CN=CC=C2N1S(=O)(=O)C1=CC=CC=C1 MOCVPCBCMCSIFA-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GKYSMAIKZJVVLO-UHFFFAOYSA-N OC(=O)c1ccc2c(c1)[nH]c1ccncc21 Chemical class OC(=O)c1ccc2c(c1)[nH]c1ccncc21 GKYSMAIKZJVVLO-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- WANUOLLLVOSMFL-UHFFFAOYSA-N ethyl 2-acetyl-4-oxopentanoate Chemical compound CCOC(=O)C(C(C)=O)CC(C)=O WANUOLLLVOSMFL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003407 synthetizing effect Effects 0.000 description 1
- PKYJYPDHSCLTJO-WHRKIXHSSA-N tert-butyl 2-deuteriopyrrolo[3,2-c]pyridine-1-carboxylate Chemical compound N1=CC=C2N(C(=O)OC(C)(C)C)C([2H])=CC2=C1 PKYJYPDHSCLTJO-WHRKIXHSSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8419029A FR2574406B1 (fr) | 1984-12-12 | 1984-12-12 | Nouveaux derives de pyrrolo-pyridine, leurs procedes de preparation ainsi que leurs applications |
| FR8419029 | 1984-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1299183C true CA1299183C (en) | 1992-04-21 |
Family
ID=9310535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000497380A Expired - Fee Related CA1299183C (en) | 1984-12-12 | 1985-12-11 | 1h-pyrrolo ¬3,2-c|pyridines and their preparation |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4831144A (ja) |
| EP (1) | EP0187631B1 (ja) |
| JP (1) | JPS61155385A (ja) |
| AT (1) | ATE56212T1 (ja) |
| CA (1) | CA1299183C (ja) |
| DE (1) | DE3579577D1 (ja) |
| DK (1) | DK576885A (ja) |
| FR (1) | FR2574406B1 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1756109B1 (en) * | 2004-05-03 | 2016-07-13 | Janssen Pharmaceutica NV | Novel indole derivatives as selective androgen receptor modulators (sarms) |
| EP2731439A4 (en) * | 2011-07-12 | 2014-12-03 | Merck Sharp & Dohme | TrkA KINASE INHIBITORS, COMPOSITIONS CONTAINING SAME, AND ASSOCIATED METHODS |
-
1984
- 1984-12-12 FR FR8419029A patent/FR2574406B1/fr not_active Expired
-
1985
- 1985-12-11 EP EP85870178A patent/EP0187631B1/fr not_active Expired - Lifetime
- 1985-12-11 DE DE8585870178T patent/DE3579577D1/de not_active Expired - Fee Related
- 1985-12-11 CA CA000497380A patent/CA1299183C/en not_active Expired - Fee Related
- 1985-12-11 AT AT85870178T patent/ATE56212T1/de not_active IP Right Cessation
- 1985-12-12 DK DK576885A patent/DK576885A/da not_active Application Discontinuation
- 1985-12-12 JP JP60280176A patent/JPS61155385A/ja active Pending
-
1988
- 1988-01-07 US US07/141,508 patent/US4831144A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3579577D1 (de) | 1990-10-11 |
| ATE56212T1 (de) | 1990-09-15 |
| FR2574406A1 (fr) | 1986-06-13 |
| DK576885A (da) | 1986-06-13 |
| EP0187631B1 (fr) | 1990-09-05 |
| JPS61155385A (ja) | 1986-07-15 |
| FR2574406B1 (fr) | 1987-02-27 |
| DK576885D0 (da) | 1985-12-12 |
| EP0187631A1 (fr) | 1986-07-16 |
| US4831144A (en) | 1989-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |